


The Best Cockslut

by NaughtyPastryChef



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Reality Show, Anal Beads, Anal Play, Anal Plug, Anal Sex, Barebacking, Blow Jobs, Bottom Dean, Comeplay, Crossdressing Dean, Dirty Talk, Dom/sub, Embarrassment Kink, Exhibitionism, Feminization, Gangbang, M/M, Moresomes, Multi, Panty Kink, Praise Kink, Puppy Play, Sex Toys, Sex for Money, Snowballing, Threesomes, and an even bigger cockslut, blow bangs, dean is a total comeslut, m/m/m/m/m/m/m
Language: English
Status: Completed
Published: 2015-01-23
Updated: 2015-01-23
Packaged: 2018-03-08 19:30:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,822
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3220733
Author URL: https://archiveofourown.org/users/NaughtyPastryChef/pseuds/NaughtyPastryChef
Summary: <blockquote class="userstuff">
              <p>Dean Winchester, notorious bottom, is offered a chance to win a million dollars. All he has to do is live in a house with 6 straight men for two weeks and convince them all to have sex with him. It's a win/win for him.</p>
            </blockquote>





	The Best Cockslut

**Author's Note:**

> OMFG, this is without a doubt the filthiest thing I have ever written. Just... for facecasting purposes:  
> John Barrowman - Jack (Torchwood)  
> Jared Padalecki - Tom (xmas cottage)  
> Misha Collins - Eric (charmed)  
> Chris Hemsworth - George (star trek)  
> Karl Urban - Vincent (the loft)  
> Chris Evans - Steve Rogers (Captain America)
> 
> Love, thanks and praise goes to Moonweaver30 on tumblr for reading this for me and babysitting me until it was out of my head and in the computer. You rock!
> 
> Also to OrgasmicDean for showing me the prompt and TaintedDean for getting the prompt in the first place and asking for someone to write it. I KNOW this has more plot than you envisioned but I hope that you still like it.

At first, there had certainly been some misgivings. Certainly, Dean liked tongues, fingers, toys, cocks, basically whatever he could fit up his ass, a lot more than the average guy. He had a “healthy sexual appetite” and was proud of his gorgeous body, but a reality tv show? It seemed more than a little awful. But, in the end he’d allowed himself to be convinced.

Two weeks of showing off his body, fulfilling kinks and wank fantasies for the viewers and trying to get a bunch of “straight” dudes to gangbang him and win a million dollars while he’s at it? What was the worst that could happen?

Dean moved into the house a day before the rest of his roommates.  He couldn’t wait to meet the men who told the station managers that they were straight; as if there was actually anyone that was 100% straight anymore. HAH.  He wandered the house, finding toys tucked in each room, most that he was familiar with and some he’d never seen anything like before.  He felt himself jump up in his jeans a little bit and decided that it couldn’t hurt to get a head start on the show. Dean gleefully stripped naked and hid all of his clothes. He wasn’t going to need them again until he was forced to leave, hopefully with a million dollars and no burning desire to work ever again.

He ran his hand across his stomach and up to his pecs, plucking at his nipples absently as he felt his cock thicken up to full hardness and bob out in front of him before he continued his exploration of the house and all it’s rooms.  He moved some toys from one room to others; he’d found a thick, gorgeous dildo in the livingroom but it was waterproof, so he moved it into the huge bathroom.  There was a plug with an animal tail hidden in one of the small bedrooms, the ones for the other guys, and he put that in the living room. If he was going to play puppy, he was going to do so for all of his watchers.

Finally done arranging and more than ready to come, he settled onto the couch in the living room with the pile of requests and kinks sent in from the potential viewers. He whistled as he read some of them over, these were some kinky fuckers for sure. He leisurely stroked his cock with one hand as he started to read the kinks aloud, not too proud to admit that a little dirty talk, even from himself to himself, helped to get him come that much harder.

Coming across the graphic description of himself with a dildo, cock and tongue in his ass all at once, he groaned and spurted come across his stomach.  He softly stroked himself through the aftershocks, watching as his come pooled onto his stomach and in his bellybutton, wishing he had the ability to lick it off himself. When his cock softened he released it, drawing his fingers through his come and bringing them up to his mouth to suck clean before he headed into his bedroom. A perfunctory wipe down and tooth-brushing and he was laying down across the giant bed that had been provided for him, closing his eyes with a smile.

It was going to be a fun two weeks.

Dean was awoken in the morning by the doorbell and he stretched as he blinked himself awake enough to get out of bed and answer the door. The first of his roommates must be arriving. Absently, he wished he’d had time for a shower, to make a slightly better first impression, but he caught sight of himself in a mirror on the way to the door and thought he didn’t really need to worry. He looked good with bed-hair and sleep soft skin.

Dean yanked open the door and took a step backwards as he was faced with all seven of his roommates. His first thought was “thank god they’re all hot” followed swiftly by “I know that one is checking me out” as they all filed into the house, some of them meeting his eyes, some of them looking at the floor and one in particular, clearly focused on Dean’s soft cock between his legs.

“Welcome. I’m sure we will all get introduced at some point, so come on in, make yourselves at home. Don’t mind me, I just got up.” Dean smiled, shutting the door behind him and putting an extra swagger in his walk as he made his way towards the kitchen, looking for some food. He needed to keep his strength up.

Two of his housemates followed him into the kitchen rather than put their stuff away and explore the house. He shook his ass as he bent over looking into the fridge, hearing a soft gasp and a cough from behind him, but otherwise ignored them until he was ready.

“Yeah?” He asked, one eyebrow raised and a smirk on his face.  The shorter dark hair one with nice smile who looked like he wanted to drop to his knees for Dean already, stepped forward, hand outstretched.

“I’m Jack and this is Tom.” He nodded at the taller, silent one standing behind him.

“You guys do know what the point of all this is, yeah?” Dean asked as he shook Jack’s hand and gave a saucy little wave to Tom. Tom flushed so prettily and Dean couldn’t help, but wonder if that blush went all the way down his body. He felt his cock start to perk up at the thought and the presence of two sexy men.  

“You gotta entice us all into a gang-bang cause we’re all straight, blah, blah, blah, boring. I’m pan, to be honest, and I’m a ringer, sent to help you. Cause, fuck Dean, they showed me your pic and I couldn’t fucking help myself. You do know that you’re fucking sexy as hell, right?” Jack asked as he crossed his arms and gave Dean an open appraisal up and down, lingering at Dean’s thickening cock.

“I’m pretty confident with myself, yeah, thanks.” Dean laughed and chugged his juice before leaving ‘Tom the mute’ and ‘Jack the ringer’ in the kitchen and making his way to his bathroom. It was going to be a long two weeks.

Day one found Dean alone for most of the day, and it was tough to search out the boys to make them watch him.  He ended up alone in the living room, working his way through the gradient butt-plug selection until he could fit the second biggest one in his lubed up hole. Knowing the cameras, at least, were on him, he sat back and rocked on it, driving it into his prostate until he came untouched all over his stomach. He lay heaving for breath on the couch until Jack wandered into the room, in what seemed to be his pajamas, taking a seat on the ottoman across from him.

“Need any help?” Jack asked laughingly.  

Dean shook his head tiredly and tried to calm his breathing. Jack’s attention didn’t help; one day in and Dean was discovering he had an exhibitionism fetish. He quirked an eyebrow and asked a silent question, remotely shocked when Jack understood enough to answer.

“The TVs in the rooms… they’re all trained to you and no one can turn it off when you’re… entertaining. We can only watch tv if you are or if you’re asleep. Even then, though, I would rather watch you.”

Dean felt a laugh forced out of him as he sat up, groaning and grinding his hips at the feel of the plug inside of him.  Jack’s eyes glazed as he watched the movements of Dean’s hips and Dean licked his lips at the bulge in Jack’s sleep pants.

“That’s not creepy at all dude. Hah, do I need to worry about my honor?” Dean laughed, standing and stretching for his audience, and privately loving all of the eyes on him.

“Do you have any, little slut?” Jack growled at him, shocking Dean and making his spent dick twitch the slightest bit.  Dean felt his come drip down his abdomen, loving how depraved and dirty it made him feel. He couldn’t wait to be covered in it.

“Not really. Who’s gonna be the biggest problem here? You’ve talked to them.”  Jack moved to the couch to get more comfortable as Dean wandered to the kitchen for a bottle of water and came back. He was shocked to see that he had more company this time, it seemed that Eric had finally ventured out of his room to see what was going on.  He looked at Dean with a cautious eye, as though Dean was going to attack him for his dick.

“Hello, Eric, right?” Dean asked, just a hint of a flirt in his voice and in his eyes as he took a seat.  Eric silently nodded and Jack sighed next to him, knowing that their talk would have to be postponed.

“Jack, I was thinking, wanna help me out with those beads in the box next to your arm there? It’s so much better when someone else puts them in.” Dean added a little sultry whine to his voice as he rolled onto his stomach on the floor, arching his back and spreading his legs so the base of the plug was visible to Eric on the couch.  Jack was rusting around in the pile of toys and viewer requests trying to find the anal beads that Dean had asked for.

As Eric watched, panting heavily and refusing to blink, Jack knelt beside Dean, rocking the plug out from his ass and groaning as he watched his slick, pink hole gape before tightening back up. One by one, Jack fed the beads into Dean’s greedy ass, as Dean’s moans grew louder and more pleading, until finally there were none left. Jack gripped Dean’s hips and shook them from side to side, allowing Dean to feel the motion of the beads inside of him.  Eric groaned as he watched precome drip from the tip of Dean’s swollen cock and fall to the floor, pooling there.

Jack, unable to wait any longer, moved until he was kneeling in front of Dean’s face, pulled down his pants and began to stroke his own cock as Dean stuck his tongue out to brush against the head with each stroke.

Jack pumped his hips in and out of his hand and groaned as he finally came all over Dean’s face, some of it landing on his outstretched tongue, but most of it across his cheekbones and even on his closed eyelids.  Eric came in his sweatpants on the couch, one hand pressed against his cock.

So, ‘Jack the ringer’ was the first to succomb to Dean.

Not much changed on day two; Steve, George and Vincent finally wandered out into the house, introducing themselves to Dean, who was playing puppy for Jack, wearing the plug with the tail and a matching set of ears they’d unearthed from the box of toys in Dean’s bedroom. Conversation was stilted, but finally began to flow when Dean got up and allowed them to watch regular tv instead of him.  

Vincent paid close attention to the way that Jack was petting Dean. Vincent whistled to get his attention, holding out his hand towards Dean. Holding down a smile, Dean relished the feeling of every set of eyes in the room on him as he crawled on all fours across to where Vincent was waiting to pet him.  George and Steve looked on avidly as Vincent petted Dean’s head, stomach, back and finally down his stomach to his cock which was hard and leaking.

“Puppy need some release?” Vincent asked, patting his knee and motioning for Dean to get up on the couch with him. Dean let his tongue loll out from his smiling mouth as he climbed up and sat on his knees next to Vincent.

“I’ve never…” Vincent whispered, and Dean tilted his head to the side and whined. Softly, he leaned forward and pressed a kiss to the side of Vincent’s soft lips.

“Do it how you like it. Or, if you want, I can stop being a puppy and do you?” Dean asked as he pulled back, keeping his lips pressed together.

Vincent nodded and leaned back, pulling his own cock out of his pants and holding it at the base. Dean licked his lips and leaned forward, letting Vincent’s pretty cock be fed to him little by little until the head was lodged in his throat and Vincent’s hips were rolling around, looking for movement.  Dean bobbed up and down, sucking for all he was worth and letting Vincent hold onto the back of his head to control the depth of his cock.  With a wet slurp, Dean pulled off and quickly turned his face and blow-job sloppy mouth up to see Vincent’s blissed out face.

“Come on my face?” Dean asked, already sliding off the couch to the floor between Vincent’s legs.  He wrapped his hand around Vincent’s wet cock and stroked, pushing his face as close as he could and sticking his tongue out to trace along his drawn up balls as Vincent pushed his hips up off the couch and came on Dean’s face.  Dean groaned, loving the feel of come on his skin, and lifted a hand to touch his own cock, which was starting to hurt.

“No, puppy. Stop that.”  

Dean’s eyes flew open to see Eric standing in the doorway with Jack, looking shocked at himself for speaking.  Dean whined and hung his head as he transitioned from his knees back to all fours and slunk across the room, to nuzzle at Eric’s legs.  He whined again and looked up at Eric, trying to plead as best he could with a dripping wet cock and someone else’s come on his face.

“Puppies don’t play with themselves like that.” Eric scolded as he walked over towards the couch, tugging Dean along with him by the scruff of his neck.  Dean silently cursed the creator of this “puppy play” game and vowed to hide the tail and ears as soon as he could. He knew he could stop the game at any time, but he also knew from secret meetings with Jack, that Eric took being a Dom very seriously and it was likely his only way to entice him into the fun. He didn’t have a problem being a sub, but he was a little tired of being a puppy.

“C’mere puppy. We gotta get you cleaned up don’t we? Vincent made a mess all over you.” Eric crooned and Dean relaxed into his hold. Eric motioned for George to come over towards them and Dean tried not to show his shock and eagerness at George’s easy agreement.

George dipped his head and licked the cooling spunk off Dean’s face,much to the surprise of everyone in the room.  Dean closed his eyes and leaned into the feel of George’s tongue on his face and the feel of his breath.  While Dean’s eyes were closed, Eric trailed his fingers down Dean’s back to “pet” his tail, and rock the plug inside Dean’s ass.

“Greedy little puppy, aren't’ you? Bet you’re just as good of a sub as you are a puppy, aren’t you?” The question was punctuated with a thrust of the plug, pulling it out to stretch Dean’s rim before plunging it back in and making him yelp and open his eyes. He turned his head around to meet Eric’s feverish eyes and whined a question at him.

“You wanna come? Gotta make sweet George there come first.” Eric demanded, punctuated by another tug on his plug.  Dean turned towards George, looking like a deer frozen in headlights.

“N-no-no thanks. I’m really okay.” George stammered, an accent rounding out the syllables.  Dean was undeterred, needing so badly to come.  He turned to look at Eric again, who was staring at George appraisingly.

“George. Be a good little sub and let the puppy get you off. I know you just want to be a good boy and do as you’re told.”  George whimpered, chewing on his bottom lip harshly. He blew a long breath out from his nose and lifted his hips off the couch to pull down his pants, exposing himself to Dean.

Dean wasted no time, licking his way up over George’s shaved balls and the underside of his cock before plunging down on the thick cock and letting it spread his lips wide open.  He worked George’s balls with his fingertips, teasing them and tickling them as he sucked the head of the man’s cock, trying to get him to come. Eric didn’t stop playing with his plug, teasing his rim and rocking it into his prostate irregularly, making Dean’s cock leak copiously.

He flicked his tongue over the bottom of George’s cock before pulling back enough to roll it over the slit and that was all George needed; his balls drew up and he shot pulse after pulse of thick cum into Dean’s waiting and willing mouth.  Dean felt a hand close over his throat before he could swallow and he turned to look at Eric, getting one last pulse over his cheekbone.

“Share it with Jack.” Eric smiled, releasing Dean’s throat and standing up to let Jack get close.

Jack slotted his mouth over Dean’s and they both groaned as they shared the salty, sticky come.  When they broke the kiss, Eric was gone, George was napping, his softening cock still outside of his pants, and Steve and Vincent were breathing heavily on the other side of the couch. Dean stood up with a groan, his cock obscenely hard. He wrapped his hand around it and came almost instantly, just narrowly missing Jack’s face.  He swayed on his feet, but stayed upright, yanking off the ears.

“No more puppy play. C’mon Jack, come take a bath with me.” Dean said tiredly, leading the way towards his private bathroom.

Four down, three really but Dean was adamant that after that performance he be able to count Eric, and three to go.

Day three sent Jack and Dean, since they were now openly a team, out into the enclosed back yard. They’d had one last session of secrets sharing, anything else that Jack had learned before being outed as on Dean’s side, in the bathroom that morning, as Dean shaved.

“Steve is super nice, and incredibly naive somehow. I dunno Dean, not sure you can change that one. Roger is gonna be your biggest challenge and here’s why. He will never meet your eye. He won’t look at you. He might not even come out of the room he’s claimed unless he knows you’re asleep. The rest of them, I don’t think there will be a problem with, but I dunno how you’ll get to him.” Dean just hummed as he checked himself out in the mirror, trying to put some thought into it, but since he had another 12 days, he couldn’t bring himself to be too worried.

Dean asked Jack to cover him in suntan lotion, cursing his pale freckled skin as Jack obliged and laughed.  Jack was naturally olive skinned and significantly more shy than Dean, refusing to naked sunbathe with him while Dean swore at him for being a coward and challenged him to a race outside.

They spent the morning lounging, waving cheery hellos to all the other men who came out to enjoy the sunshine. Dean really enjoyed it when George, Steve and Tom stripped down to shorts and nothing more for some exercise.  Tom had muscles for days, and at 6’5” was easily taller than everyone else in the house.  Dean couldn’t stop staring as Tom’s hair darkened with sweat and trails of sweat formed in the ridges and grooves of his naked torso. Jack leaned over to talk as they blatantly stared.

“Damn. You are one lucky slut; these are the nicest views I’ve gotten in a long time.” He whispered, both of their head turning to watch when George walked to the edge of the small in-ground pool and dove in, back muscles rippling all the while.  Steve and Tom kept working out, working with each other and getting even more sweaty as the sun beat down and the day heated up around them.

“I can’t even decide if there’s one I like the most, you know? I mean there’s Steve… looking hot as hell in that all American, blonde haired, blue eyed kinda way. Tom, damn, I don’t even need to explain why he draws the eye, have you seen his hands? He must have a monster cock.  George is just classically handsome and when you add in the accent and everything else. Oh man, I may not make it out of this alive, but Jacky boy, what a damn way to go.” Dean sighed dreamily, sounding more like a teenage girl with a crush than a cockslut looking for sex.

Jack squinted at him before pulling his sunglasses back down over his eyes and adjusting himself in his swim trunks.

“Time to roll over and reapply or head inside you pale, freckled bitch, or you’re not gonna be good for anything.” Jack said saucily as Dean sat up and began cursing at the pull of his overheated skin.  Dean’s cock bobbed in front of him as he marched into the house. In the kitchen he was greeted with stares from Vincent and Eric as he marched towards the fridge and grabbed a bottle of water. He kept his eyes on the two men, who seemed to be frozen by his mere presence, as he gulped it all down.

“Boys. Make sure to eat lots of fruits and veggies. Makes your come thick and sweet for me.” He winked and blew a kiss before heading into his bedroom, throwing himself onto his bed and laying his head on his folded arms as he contemplated the ceiling and the problem of Roger.  He fell asleep with no real solution, but a partially formed plan in his head.

Dean was coming out of his slumber when he was awoken by a soft knock on his door that turned out to be Tom and Steve, asking if he’d like to have dinner with them, and only them. He shot them his brightest smile and agreed, pleased to be asked to dinner, even if he’d be more pleased to be fucked within an inch of his life. He missed having a cock in his ass.

“Can you-could you wear something?” Steve stammered, not blushing but somehow looking like he wanted to. Dean frowned and looked at the closet where he’d hidden his clothes.

“N-n-not that we don’t like looking at you but we both g-g-get a little tongue tied when you’re naked.” Steve added as quickly as he could with Tom nodding his head so hard that he looked like a bobble head.

“If it means I can get a few works out of both of you, then yeah, I can do that. Meet you in an hour?” He asked, already trying to decide what he could wear that would be enticing yet covering.

“An hour would b-b-be great. W-w-we set up a table in the back yard.” Steve stammered cutely before he and Tom backed out of the room and shut the door, leaving Dean to himself.

An hour later saw Dean making his way back to the back yard wearing his oldest Metallica tee-shirt, soft and nearly see through with age, and his favorite jeans, the ones that hugged his ass in all the right places and cupped his cock lovingly after years of wear. Bare feet and artfully tousled hair completed the ensemble and Dean thought he looked just as good now as he had when he was naked.  Jack’s appreciative wolf-whistle and dirty words on his way out of the living room had helped too.

Dinner was modest food and good company and excellent beer. Both Tom and Steve were able to talk without stuttering and while looking Dean in the eyes. He thought it was cute,really, that they wanted to wine and dine and seduce him when he was a sure thing, but by the end of dinner, he began to really appreciate that they’d taken the time to get to know him.

The three of them cleaned up, doing dishes and cleaning the kitchen before Tom and Steve walked Dean back to his room. When they reached the bedroom door, Dean shoved it open and raised an  eyebrow questioningly.

“N-n-not a no, but not tonight.” Steve stammered, confusing Dean totally. His objection was cut off by Steve’s lips, pressing against his briefly before he whirled around and walked away.  Dean turned to Tom and his heart rate sped up at the look on the taller man’s face.

“Hell yes.” Tom said, reaching down and lifting Dean off his feet, his hands cupping Dean’s ass as Dean wrapped his legs around Tom’s waist.  Tom slammed Dean up against the wall, forcing a grunt out of him before ducking his head and taking Dean’s lips in a fierce kiss. He trailed his tongue along the seam of Dean’s lips and Dean opened to him with a groan, greedily sucking Tom’s tongue into his mouth before letting it go to nibble at his lips.

“I wanna fuck you. Am I allowed to fuck you?” Tom asked as Dean rolled their bodies together, whimpering at the long line of heat on his stomach that had to be Tom’s dick.

“Fuck yes, I miss having a cock in me. Please fuck me.” Dean whined, pulling at Tom’s shirt ineffectually.  Tom pulled him off the wall and turned to take the few steps into Dean’s room, practically throwing him onto the bed. They busied themselves with ripping off their own clothes, not noticing until the were both naked that Jack and George were in the room.

“Oh, don’t mind us. We were just waiting for Dean to get home from his date, but we can leave if you...holy shit, your cock!” Jack exclaimed when he caught sight of Tom’s dick, standing tall and proud and nine inches of gorgeousness.

“You can stay.” Tom growled, kneeing his way onto the bed to hover over Dean, a contemplative look in his eye.  He turned to look at Jack and George again.

“In fact...why don’t you help?  George, fuck his face, make him sloppy. Jack, prep his ass for me while I watch.”  Tom rolled onto his side, shoving Dean with one arm so that he was farther away on the big bed and there was enough room for the other two to join them.

Tom reached down and palmed his balls, groaning as Jack pressed Dean’s knees up to his chest and ducked his head down to start rimming him.

“Oh fuck, you’re just as dirty and slutty as he is, aren’t you? Does his ass taste good? I’ll just bet it does. Look at you, tongue and fingers all up in his dirty-sweet asshole. Push his leg up a little bit more so I can see a little better? Yeah, fuck, just like that.”  

Dean moaned around George’s cock at the running commentary from Tom and the feeling of Jack’s tongue in his ass. It had been so long since he’d been rimmed properly that he had forgotten just how good it felt.  Dean relaxed his jaw as best he could and let George fuck his face as Tom had ordered, precome and spit bubbling out the corners of his mouth and down his cheeks and reflexive tears streaming from his eyes. It felt so good but he wanted more in his ass, more come more everything. He whined through his nose when George pulled out and rolled his hips down into Jack’s face.

“He’s an eager slut. Has he had a cock that wasn’t made of plastic in his ass since he got here?” Tom asked, his hand speeding up on his cock and a flush spreading down his neck and onto his chest.

Dean tapped at George’s hip to have him pull out so that he could take a deep breath and answer Tom.

“No, nothing that wasn’t made of plastic. And Fuck, your dick is gonna feel so good splitting me open.”  Dean’s voice was rough, and as soon as the last word was out of his mouth, he was pulling on George’s amazing ass to get his thick cock back into his mouth.  George yelled out when the head of his cock bumped the back of Dean’s throat again, and he was pulsing and shaking, coming in Dean’s greedy mouth.  He gently pulled his dick out of Dean’s mouth and rolled away to watch the show.

“Jack, that’s enough.” Tom practically snarled as he impatiently shoved Jack from between Dean’s legs and pressed the head of his cock at Dean’s puffy, shiny rim.  He pressed forward, sinking in easily until his balls were nudging at Dean’s. He rolled his hips experimentally, both he and Dean groaning with pleasure as his cock pressed at Dean’s prostate, making his hole clench.

“Fuck me dammit, hard and fast. Hurt me a little.” Dean whined and Tom could do nothing, but comply. He rolled his hips back, pulling out smoothly before slamming back inside and setting up a punishing rhythm that had Dean grunting out wordless sounds and the satisfying sound of flesh slapping together filled the air. Tom reached down and gripped Dean’s short hair, pulling his head up and bending Dean nearly in half as he smashed their lips together in a near-violent kiss.

“Come for me now.” Tom said as he pulled back from the kiss, keeping eye contact with Dean.

Dean felt his body spasm as it followed Tom’s orders, clenching tight and coming totally untouched.

Tom thrust through Dean’s orgasm, allowing it to draw his own to the edge.  He left Dean’s slack body fall back to the bed and pulled out, jacking his cock a few more times before coming on Dean’s cock and stomach, striping his pale torso with white. Then he fell to the bed, his face smashed in Dean’s shoulder as they both tried to get their breathing under control.

“Tom, you and Eric need to get together. Between your dirty mouth and toppiness and his dirty mouth and Dominance, you two could rule the fucking world. Doesn’t hurt that you’re both fucking sexy, either.” Dean mumbled into Jack’s stomach, his head having been pulled there a moment after he came.

“Mmmhmmm, tomorrow. Sleep now bitch.” Was Tom’s brilliant reply, that and a tiny snore that Dean, god help him, labelled cute as he drifted into an exhausted sleep.

Dean let Steve take him on another “dinner date” before pressing the issue and dropping to his knees and sucking his cock.  Steve looked vaguely horrified until Dean looked up, caught his eye and winked. After that, Steve trailed Dean around the house like a puppy, eager to do his bidding in any way.  Dean thought it was cute, though he didn’t really need a shadow.

Roger remained an enigma. One week in and Dean had slept with or blown everyone except for Eric and Roger, and he was no closer to finding a solution to other of these problems.

Eric was such a Dom but, Dean just couldn’t figure out what turned him on.  He played the part of the perfect little sub, doing whatever was commanded of him, in most cases gleefully. And He knew that Eric wanted him, since he’d come in his pants watching Jack feed anal beads into his ass that first day. He knew that Eric liked to command and he really liked to watch, so Dean decided all sexual activities be in the common areas of the house.

George was still too shy to fuck him, but loved to fuck Dean’s throat making Dean wander around all the time talking like he’d been swallowing glass.  Steve and Tom took turns having Dean sit on their cocks while they sat in the living room together, not fucking him, just keeping him open and letting him cockwarm for them.

Roger still hadn’t let himself get caught in the same room as Dean by day eight, and Dean was getting desperate.  He headed into his room, into the closet where his duffel bag sat, unopened since that first date with Tom and Steve.  Taking a deep breath, Dean pulled out his most prized possessions from the bottom of the bag. These were his very favorite things in the world and something he’d never shared with anyone.  He lay everything out on the bed and headed into his bathroom to get ready; it was going to take a while.

Considering what he’d done in the last week alone, Dean was nervous as he stood at the door to Roger’s room,his hand raised and poised to knock.  He cleared his throat and looked behind himself nervously before he dropped his robe to the floor and knocked loudly on the door. He heard a soft “come in” from the other side of the door and opened it pushing inside with his head down until he could shut the door behind him.  As soft gasp greeted him when the door was shut.

Dean looked up and caught the eyes of the last man who hadn’t come to play with him and made him finally pull out all the stops to make it happen.  Dean’s legs rubbed together, smooth and hairless under his pleated miniskirt. He tugged at the short hem, knowing that as he tugged it down in the front it exposed more of his ass in the pink, silk panties.  He wore a white collared shirt, easily two sizes too small for him and exposing lots of skin at his navel.

“I thought..” Dean started, uncharacteristically shy, but he was sharing something with Roger that he’d never shared before.  Roger was the first person ever to see Dean dressed like a pretty little slut.

“Shut up.” Roger said, slashing his hand through the air at Dean as he stood up from his bed. He stalked towards Dean, his face an unreadable mask.  He circled Dean, sucking in a deep breath as he passed behind him and saw the panties covering Dean’s ass.

“You want it that bad? You’re willing to play the pretty girl?” Roger breathed, getting right into Dean’s face as he asked.  Dean bit his lip and nodded as he looked down at his fingers, toying with the pleats on his skirt.

“Such a pretty girl. Pretty girls get what they want. What do you want, my pretty girl?” Roger asked, his cock an obvious tent in his pants.  Dean chewed his lip a little more, screwing up his courage as he tried to make his voice not shake.

“Fuck me with my skirt on?  I’m so wet for you already, just bend me over, pull my panties to the side and fuck me?” His voice didn’t waver as he asked, but he couldn't make eye contact as he asked.  He felt Roger’s finger under his chin, tilting his head up to look him in the eye.

“Pretty girl. My good, pretty girl. You’ll get what you want. You’re all wet for me baby girl?” Roger crooned at him, and Dean felt his knees go weak as he nodded silently.

“Go face the bed, pretty girl, and bend over so I can see that ass in those pretty panties.” Dean nodded and went over to the bed, bending over and pushing his ass out as he lay his hands flat on the bed and waited. He could feel his skirt in the back halfway up his ass, exposing almost his whole ass and his face flamed.  A fingertip dragged along the skin of his hip, exposed by his position and his panties and he waited and felt his heart jack-hammer in his chest.

He felt Roger’s fingertips trail along the exposed skin of his lower back, making him shiver. The teasing touches vanished and Dean arched his back, wordlessly asking for more.

“Oh my pretty girl, you want more? You need more? Such a pretty little slut, all bent over and begging for my cock. Are you wet for me baby girl?” Roger rambled into the back of Dean’s neck, making Dean writhe and gasp. Roger’s fingertips found their way up the back of Dean’s thigh and over the back of his ass, practically caressing the satin of his panties.  He felt the material roughly yanked to one side, exposing his hole, prepped and aching to be filled. Roger let his fingertip dip to caress Dean’s rim, as Dean forced the muscle to relax.

“You are wet for me baby girl. You want it bad, huh? Want my cock? Will that make you feel better, my pretty, dirty girl?”  

Dean nodded and flexed his asshole again, trying to draw in Roger’s fingertip, but it stayed stubbornly outside of his body.  Both hands left him suddenly and he heard the sound of a zipper; he tried to whip his head around to get a glimpse of Roger’s cock, but Roger slapped his ass through the satin, making him wince, before the satin was pulled aside again.

“No baby girl, you can get a glimpse when I let you and no sooner, yeah?”  Roger husked as he traced the tip of his cock around the edge of Dean’s rim, getting the area wet with his precome.  He pressed at the center of Dean’s pink hole, moving forward slowly without stopping until it opened up and let him inside.  He bottomed out with one thrust, holding Dean’s hips still as he let Dean adjust to him.

“I’ve been watching you, you know. Am I the only one that you’re willing to be a pretty girl for? Hmm? How about Eric, wanna be a pretty girl for him too? Want him to come and fuck your pretty mouth, palm your flat little tits while I make you all sloppy back here?”

Dean mewled, whimpering, practically crying at the images from Roger's dirty words. He wanted it, he wanted it so badly. The two men he’d not gotten his hands on, taking him at once.  He couldn’t imagine anything better and he tried to convey that to Roger with his body, words being beyond him.

“Want me to get Eric in here? Play with your tits and fuck your face while I take what I want from you? You won’t be such a pretty girl when we’re done; you’re gonna be a mess, aren't you baby girl?” Roger punctuated each question with a rough, irregular thrust, shoving Dean’s body back and forth on his cock as though he weighed no more than a ragdoll.

“ERIC!” Roger shouted suddenly, freezing his whole body with his cock half-way inside of Dean’s greedy ass.  The door opened and shut behind Dean, and he resisted the impulse to turn and look, knowing he wouldn’t be allowed.

“What do we have here?” Eric’s voice rang out and Dean began to tremble with excitement. He wanted to be a pretty girl for Eric too.

“Turn around and look at him pretty girl, ask him for what you want?” Roger grunted, letting up on the pressure on the back of Dean’s neck so that he could do so.

Dean turned his head around, trying to find his voice to ask Eric for what he needed. He licked his lips and looked up the length of Eric’s body, dying to get his hands on what was underneath those clothes.

“Please Eric, fuck my mouth. Play with my tiny tits and fuck my mouth while he fucks my tight pussy.  I need it so bad. I wanna be your pretty girl.” Dean whined at Eric, loving the way that he could see the darkening of the man’s eyes and the way that his cock clearly twitched in his pants.  Dean risked taking a hand off the bed, even though he hadn't been given permission, to reach out and beckon Eric forward.  Roger threaded his fingers through the short hair at the back of Dean’s head and yanked as hard as he could, causing Dean’s ass to arch up into his rough thrusts.

“Okay pretty girl. You beg so beautifully, but I’ll bet that even when you’re a sloppy messy with our come, you’re still the prettiest girl. Roger, stop so I can get underneath our baby girl, yeah?” Eric asked offhandedly and Dean could feel the tremble through Roger’s body at the will it took to hold back.

Eric slid smoothly underneath Dean, palming his small tits before shifting around so that Dean could open up his pants and pull out Eric’s cock. Dean’s mouth was filling with saliva at the thought of finally getting it in his mouth, tasting Eric like he’d wanted since that first day when he’d watched the anal bead play.

Dean gathered saliva in his mouth and spat it at the base of Eric’s exposed cock, before smoothing it up the shaft with his palm.  He pursed his lips and pressed them to the damp tip of Erics cock, just as pretty and delicious as he’d thought it would be, kissing as he lapped up the hint of precome gathered there. Wanting more, he parted his lips and slipped them over the whole head, curling his tongue underneath it, concentrating on the bundle of nerves under the head.  His hand was still steadily stroking the shaft when Roger grabbed his hips hard and decided to get his attention back by slamming in and out of him hard, muttering filth all the while. Dean’s cock was bouncing in his panties, the tip popping out over the waistband until it was leaking all over his stomach.  He whined around the thick cock in his throat, making Eric shudder and slide his hand into the collar of Dean’s shirt, rubbing his palm across his puffy, swollen nipples.

“Roger’s gonna stuff you full and breed you up pretty girl. Do we have a plug nearby? He’s gonna breed you good and then plug you up. If you do a really good job, then maybe I’ll breed you up too, baby girl. You want that?” Eric groaned at the back of Dean’s head as it bobbed up and down in his lap. The only reply he got was another keening moan around his cock and the flash of lust-blown green eyes.

Roger slammed his hips forward, grinding into Dean’s ass as his cock spasmed and he came deep inside Dean, his hips never stopping their grinding motions.  Dean felt like he was going to combust when he felt Roger’s hot come filling him up.  He redoubled his efforts on Eric’s cock, twisting his hand around the base as he relaxed his jaw and pushed himself as far down as he could go.

Roger pulled out and watched as Dean’s hole gaped open, trickling come.  He wiped up the trail of come and lube. He pressed it back inside of Dean as he looked for the plug that he knew had been hidden in his room. He winked at Eric as he slid it inside of Dean, wondering if it would even make a difference because it was so small.  He groaned and felt his soft cock twitch as he watched Dean’s hole flex around the plug and clench to keep it inside of him.  He moved to pet Dean’s hair and whisper in his ear.

“You are my good, pretty girl. You take good care of Eric now, okay baby girl?”

Dean’s eyes rolled back into his head with the endearment and the soft touches.  His cock was throbbing so much that it hurt and he took his mouth off Eric’s cock to beg for release.

“Please, can I come? I need to come! I just...just touch me a little? Rub me, or can I rub..”  He panted, breaking off unexpectedly when Eric came on his face, across the bridge of his nose and into his hair.  He whimpered sadly, angling to try and get the next pulse into his mouth even as his hips wiggled, looking for some kind of relief for his cock.

“Come baby girl. Do it now, just cause I told you to.” Eric huffed out, letting Dean ease him through his orgasm and suck the come right out of the tip of his cock.

Amazingly, Dean did.  He felt his whole body twitch as he came, ruining the inside of his panties and skirt as pulse after pulse of come stained them both.

“Don’t change, don’t put the robe back on over your clothes; walk back to your room, leave the plug in your ass and take a shower. I have a surprise for you tonight, after we all have dinner.” Eric said softly, caressing the side of Dean’s cheek.  

Dean resisted the urge to nuzzle into the touch; affection he got from Jack and George, but sex is all he got from the rest of them.  He straightened up from his position on bed, pulling the skirt down over his ass and making his way to his room to do as he’d been told.  He thought he might know what the surprise was, but he didn’t want to ruin it.

An hour later found Dean in the living room on his knees again. This time, the biggest plug in the house is in his ass, keeping him open and holding three loads of come inside his greedy hole while he gets splattered with come from the six men jerking off over his upturned face.  He wishes he could have a cock in his ass and another in his mouth at all times, which with an even number of roommates should be possible, but Eric was in charge and he’s wanted to see Dean like this. A greedy, perfect cockslut covered in mingled come from all of the roommates at once. Dean could see a reflection of himself in the mirror that one of his lovely straight boys had brought into the living room and he had to partially agree with Eric; it was a beautiful sight.

At the end of two weeks, Dean, used and abused and loving it, put his clothes back on, twitching because it felt wrong to cover himself.  He won the game, collected his check and headed home. He had three phone numbers, five kik and an actual date set up with Tom, who shockingly lived less than thirty minutes from him.

Dean Winchester is the best cockslut.

 

 


End file.
